WO2001035918A1 - Mint flavor and aroma compositions - Google Patents

Mint flavor and aroma compositions Download PDF

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Publication number
WO2001035918A1
WO2001035918A1 PCT/US2000/031266 US0031266W WO0135918A1 WO 2001035918 A1 WO2001035918 A1 WO 2001035918A1 US 0031266 W US0031266 W US 0031266W WO 0135918 A1 WO0135918 A1 WO 0135918A1
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WO
WIPO (PCT)
Prior art keywords
cysteine
composition according
flavor
oil
mint
Prior art date
Application number
PCT/US2000/031266
Other languages
French (fr)
Inventor
Lawrence L. Buckholz, Jr.
Brian Byrne
Original Assignee
J. Manheimer, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by J. Manheimer, Inc. filed Critical J. Manheimer, Inc.
Priority to AU16076/01A priority Critical patent/AU1607601A/en
Publication of WO2001035918A1 publication Critical patent/WO2001035918A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • This invention relates to mint flavor and aroma compositions and coolant compositions suitable for use in foodstuffs, tobacco products, fragrances and pharmaceuticals. This invention also relates to a process for preparing the inventive compositions.
  • Mint oils and mint flavors are used to flavor confections (sugar candy, breath mints, chewing gum etc.), as well as oral care products ( toothpaste, mouthwash, etc.), tobacco and smoking articles ( snuff, cigarettes, etc.).
  • Mint oils are used to fragrance topically applied materials (perfume, lip balms, lotions, etc.), as well as other fragrance applications (room deodorizers, soaps, cleaning products, etc.).
  • Mint oils and mint flavors are used to deliver topical cooling in the oral cavity (mouthwash, chewing gum etc.) as well as on the skin (colognes, lotions, bandages etc.) SUMMARY OF THE INVENTION
  • Mint oils, mint flavors and flavors containing chemical components found in mint are used widely in flavoring edible substances and topically applied materials.
  • the present invention provides for the treatment of such oils and flavors with cysteine, its salts, precursors or derivatives thereof.
  • the resultant product possesses properties which include: a) a stronger mint flavor; b) enhanced sweetness; c) more fresh picked flavor; d) a stronger cooling effect; and e) a creamy rich mouthfeel.
  • the products of this invention allow one to use lower concentrations of mint flavors or oils in products to achieve these effects with the product additionally possessing greater fresh picked character, cooling and creamy mouthfeel.
  • a greater flavor strength and impact can be achieved without the bitterness associated with high menthol containing products.
  • the products of this invention may be used in coolant compositions.
  • the inventive flavor compositions provide for a mint flavor stronger in flavor and enhances the sweetness in edible compositions.
  • the mint flavors are fresher (more characteristic of fresh picked mint), with a stronger cooling effect.
  • a secondary characteristic is the development of a creamy rich mouthfeel which compliments the above organoleptic sensations
  • the cysteine flavor or aroma compositions of the present invention comprise a treated mint oil, flavor or aroma obtained by mixing said mint oil flavor or aroma with cysteine, a salt or ester thereof, a cysteine precursor or a cysteine derivative, optionally in the presence of a solvent.
  • the process by which the treated mint flavors or aromas are obtained vary in time, temperature, solvent and source of cysteine. How this is achieved is limited to the resourcefulness of those skilled in the art and not meant to be the limiting factor of this invention
  • the temperature for the mixing process may range from low temperatures to high temperatures and the process may be conducted under atmospheric conditions or pressure. In a preferred embodiment, the temperature for the process may range from room temperature (about 20°C) to about 110°C. Depending upon the source of cysteine and contact time needed to complete the process, temperatures above 110°C to about 250°C, with commensurably shorter contact times, may be used.
  • This source of cysteine in the present invention includes cysteine itself, as well as its salts and ester forms. Preferred are the inorganic and organic salts of cysteine, with cysteme hydrochloride being especially preferred.
  • carboxylic acid alkyl esters of cysteine are also preferred.
  • these sources of cysteine are well known in the art and are obtained either commercially or by processes known in the art.
  • the source of cysteine may also be precursors of cysteine, such as its amino acid esters. Again, these precursors are well known in the art and are obtained either commercially or by processes known in the art.
  • Derivatives of cysteine include the cysteine adducts obtainable by the reaction of cysteine or an ester or salt thereof with an ⁇ , ⁇ -unsaturated carbonyl-containing compound. These adducts are described in copending application USSN 09/440,591, entitled Flavor Freshness Enhancers, herein incorporated by reference.
  • the mint flavor and aroma compounds for the invention and aroma compounds can be, for example, mint oils or flavors made from mint oil. These flavor and aroma compounds can be artificial or derived form natural sources, whether crude, purified or fractionated.
  • the mint flavor and aroma compositions are well know in the flavor art and may be obtained commercially or through processes known in the art.
  • the ratio of substrate oil or flavor to cysteine can be varied to achieve a particular economic goal, but is not limited to large excesses of one ingredient or the other.
  • cysteine be used in parts per million to a one to one weight ratio to the mint oil.
  • cysteine When treating distilled whole mint oils it is economically advantageous to treat about 99.9 parts of mint oil with about 0.1 parts cysteine with the product being used directly "as is".
  • cysteine In the case of highly purified fractions, nearly one to one ratios of cysteine to the fraction are most effective, with the product being further diluted in other flavors or oils to impart an enhanced sweetness, flavor strength and coolness.
  • a wide range of solvents may be used in the inventive process.
  • the solvents include those which are commonly used in foodstuffs, cosmetics and pharmaceutical preparations. It is also possible to use non-edible solvents, provided that they are removed by a removal step.
  • ethanol, water or mixtures thereof are used as solvents. Also preferred is the use of no solvent.
  • the pH can be varied depending upon the solvent used, if any, and the cysteine source. Other considerations are conditions necessary to generate cysteine from a precursor or derivative.
  • the preferred embodiment is a pH of about 1 to about 10, although, this is not intended to limit the scope of the invention.
  • inventive mint flavor and aroma compositions may also be formulated in coolant compositions where the inventive compositions are combined with other coolant materials. It is well known in the art e.g. U.S. Patent 5,451,404 and references cited therein all herein incorporated by reference, that multiple coolants synergize and amplify the cooling of single coolants. The present compositions also synergize and amplify the effect of single coolants.
  • the coolants which may be used in these compositions, are well known in the art and may be obtained commercially or through a known process.
  • Suitable coolants include, for example, menthol, N-ethyl-p- methane-3-carboxamide (WS-3), N-2,3-trimethyl-2-isopropyl butamide (WS-23), 1- menthone glycerin ketal, 3-1-menthoxy propane- 1,2-diol or monomenthyl succinate or its salts.
  • Such compositions, as well as the amount of mint flavor or aroma to add to these compositions is well known to one skilled in the art.
  • the mint flavor and aroma compositions may be used in a wide range of products and fragrances such as of foodstuffs, tobacco products, pharmaceuticals, oral care products, and sweeteners.
  • Such products, as well as the amount of flavor or aroma to add to these products would be well known to one skilled in the art.
  • Especially preferred food products include confectioneries such as chewing gums.
  • Especially preferred oral care products include mouthwashes or toothpastes.
  • Example 2 The above ingredients were added to a 500 ml round bottom flask equipped with a reflux condenser, mechanical stirrer and pot thermometer. The contents were heated over 20 minutes to a temperature of 104°C and the temperature held for one hour. The contents were cooled to room temperature and the phase separated. The treated spearmint oil was used as is.
  • Example 2 The above ingredients were added to a 500 ml round bottom flask equipped with a reflux condenser, mechanical stirrer and pot thermometer. The contents were heated over 20 minutes to a temperature of 104°C and the temperature held for one hour. The contents were cooled to room temperature and the phase separated. The treated spearmint oil was used as is.
  • Example 2 The above ingredients were added to a 500 ml round bottom flask equipped with a reflux condenser, mechanical stirrer and pot thermometer. The contents were heated over 20 minutes to a temperature of 104°C and the temperature held for one hour. The contents were cooled to room temperature and the phase separated. The treated spear
  • a solution of treated spearmint oil from Example 1 was made by using 0.1 g treated spearmint oil with 9.9 g ethanol.
  • Example 4 Product of Example 3 was compared against the untreated product as in Example 2.
  • the treated peppermint oil was stronger, sweeter and cooler than untreated oil.
  • Example 1 The above ingredients were treated as in Example 1.
  • the product of Example 5 were evaluated as in Example 2.
  • the treated carvone, product of Example 5, was sweeter, stronger in flavor, fresher tasting and surprisingly was cool tasting relative to the untreated material.
  • Chewing gum compositions were prepared using the formulations set forth below. The formulations were prepared by melting the gum base at a temperature of about 85 to 90°C and then adding with mixing the lecithin followed by adding the corn syrup and
  • Example 9 had high up front cooling which maintained for 15 minutes without bitterness development. Flavor was also stronger than Example 8 with a lingering sweetness for 12 minutes.
  • Example 12 Product of Example 11 had high up front cooling which maintained for 15 minutes without bitterness development. Flavor was also stronger than Example 10 with a lingering sweetness for 12 minutes.
  • Example 12
  • Example 13 The above ingredients were treated as in Example 1 and evaluated as in Example 2.
  • the treated Fennel Oil was stronger in anethol notes, was sweeter and more cooling than the untreated material.
  • Example 13 The treated Fennel Oil was stronger in anethol notes, was sweeter and more cooling than the untreated material.
  • the treated peppermint oil was stronger in peppermint flavor, sweetness and coolness than untreated peppermint oil.
  • Example 14 The above ingredients were treated as in Example 1 and the product evaluated as in Example 2.
  • the product of Example 14 was stronger, sweeter and cooler than the untreated oil and was similar in character and strength to the product of Example 1.

Abstract

This invention relates to mint flavor and aroma compositions suitable for use in foodstuffs, cosmetics, fragrances, sweeteners and pharmaceuticals. This invention also relates to a process for preparing the inventive compositions.

Description

TITLE OF THE INVENTION
MINT FLAVOR AND AROMA COMPOSITIONS
RELATED APPLICATIONS
This application is related to application USSN 09/438,243, filed November 12, 1999, entitled Citrus Flavor and Aroma Compositions, and to application USSN 09/440,591, filed November 15, 1999, entitled Flavor Freshness Enhancers, both filed concurrently herewith and both of which, as well as all documents cited in those applications and those cited herein are hereby incorporated by reference.
FIELD OF THE INVENTION This invention relates to mint flavor and aroma compositions and coolant compositions suitable for use in foodstuffs, tobacco products, fragrances and pharmaceuticals. This invention also relates to a process for preparing the inventive compositions.
BACKGROUND OF THE INVENTION There is constant interest in improvement of mint flavor. Several approaches have been used to strengthen the flavor and thereby lower the burning and bitterness associated with higher use levels. This has been achieved in part by adding multiple cooling compounds so as to lower the use of menthol and menthol-containing mint oils. By nitrogen sparging peppermint oil to remove the undesirable lower boiling aldehydes and dimethyl sulfide, a smoother, stronger tasting flavor is achieved. Yet another approach has been to encapsulate the mint flavor and cooling agents to reduce the initial bitterness and prolong the effect of cooling, especially in chewing gum applications.
Mint oils and mint flavors are used to flavor confections (sugar candy, breath mints, chewing gum etc.), as well as oral care products ( toothpaste, mouthwash, etc.), tobacco and smoking articles ( snuff, cigarettes, etc.). Mint oils are used to fragrance topically applied materials (perfume, lip balms, lotions, etc.), as well as other fragrance applications (room deodorizers, soaps, cleaning products, etc.). Mint oils and mint flavors are used to deliver topical cooling in the oral cavity (mouthwash, chewing gum etc.) as well as on the skin (colognes, lotions, bandages etc.) SUMMARY OF THE INVENTION
Mint oils, mint flavors and flavors containing chemical components found in mint are used widely in flavoring edible substances and topically applied materials. The present invention provides for the treatment of such oils and flavors with cysteine, its salts, precursors or derivatives thereof. The resultant product possesses properties which include: a) a stronger mint flavor; b) enhanced sweetness; c) more fresh picked flavor; d) a stronger cooling effect; and e) a creamy rich mouthfeel.
The products of this invention allow one to use lower concentrations of mint flavors or oils in products to achieve these effects with the product additionally possessing greater fresh picked character, cooling and creamy mouthfeel. Alternatively, at normal concentrations of mint, a greater flavor strength and impact can be achieved without the bitterness associated with high menthol containing products. When used in chewing gum, a prolongation of the flavor during the chewing process is an added advantage. Moreover, the products of this invention may be used in coolant compositions. The inventive flavor compositions provide for a mint flavor stronger in flavor and enhances the sweetness in edible compositions. Additionally, in edible applications, the mint flavors are fresher (more characteristic of fresh picked mint), with a stronger cooling effect. A secondary characteristic is the development of a creamy rich mouthfeel which compliments the above organoleptic sensations These and other embodiments are disclosed or are obvious from and encompassed by the following Detailed Description.
DETAILED DESCRIPTION The cysteine flavor or aroma compositions of the present invention comprise a treated mint oil, flavor or aroma obtained by mixing said mint oil flavor or aroma with cysteine, a salt or ester thereof, a cysteine precursor or a cysteine derivative, optionally in the presence of a solvent. The process by which the treated mint flavors or aromas are obtained vary in time, temperature, solvent and source of cysteine. How this is achieved is limited to the resourcefulness of those skilled in the art and not meant to be the limiting factor of this invention
The temperature for the mixing process may range from low temperatures to high temperatures and the process may be conducted under atmospheric conditions or pressure. In a preferred embodiment, the temperature for the process may range from room temperature (about 20°C) to about 110°C. Depending upon the source of cysteine and contact time needed to complete the process, temperatures above 110°C to about 250°C, with commensurably shorter contact times, may be used. This source of cysteine in the present invention includes cysteine itself, as well as its salts and ester forms. Preferred are the inorganic and organic salts of cysteine, with cysteme hydrochloride being especially preferred. Also preferred are the carboxylic acid alkyl esters of cysteine, with the methyl, ethyl, propyl, isopropyl, butyl and isobutyl ester being most preferred. These sources of cysteine are well known in the art and are obtained either commercially or by processes known in the art.
The source of cysteine may also be precursors of cysteine, such as its amino acid esters. Again, these precursors are well known in the art and are obtained either commercially or by processes known in the art. Derivatives of cysteine include the cysteine adducts obtainable by the reaction of cysteine or an ester or salt thereof with an α,β-unsaturated carbonyl-containing compound. These adducts are described in copending application USSN 09/440,591, entitled Flavor Freshness Enhancers, herein incorporated by reference.
The mint flavor and aroma compounds for the invention and aroma compounds can be, for example, mint oils or flavors made from mint oil. These flavor and aroma compounds can be artificial or derived form natural sources, whether crude, purified or fractionated. The mint oil, refined mint oil, fractionated mint oil or a portion of a mint oil after fractionation, as well as a blend of oils or a compounded mint oil either natural or artificial, for example, natural cornmint oil rectified, plus menthol (artificial). The mint flavor and aroma compositions are well know in the flavor art and may be obtained commercially or through processes known in the art. The ratio of substrate oil or flavor to cysteine can be varied to achieve a particular economic goal, but is not limited to large excesses of one ingredient or the other. It is the preferred embodiment that cysteine be used in parts per million to a one to one weight ratio to the mint oil. When treating distilled whole mint oils it is economically advantageous to treat about 99.9 parts of mint oil with about 0.1 parts cysteine with the product being used directly "as is". In the case of highly purified fractions, nearly one to one ratios of cysteine to the fraction are most effective, with the product being further diluted in other flavors or oils to impart an enhanced sweetness, flavor strength and coolness. A wide range of solvents may be used in the inventive process. The solvents include those which are commonly used in foodstuffs, cosmetics and pharmaceutical preparations. It is also possible to use non-edible solvents, provided that they are removed by a removal step. In a preferred embodiment, ethanol, water or mixtures thereof are used as solvents. Also preferred is the use of no solvent. The pH can be varied depending upon the solvent used, if any, and the cysteine source. Other considerations are conditions necessary to generate cysteine from a precursor or derivative. The preferred embodiment is a pH of about 1 to about 10, although, this is not intended to limit the scope of the invention.
The inventive mint flavor and aroma compositions may also be formulated in coolant compositions where the inventive compositions are combined with other coolant materials. It is well known in the art e.g. U.S. Patent 5,451,404 and references cited therein all herein incorporated by reference, that multiple coolants synergize and amplify the cooling of single coolants. The present compositions also synergize and amplify the effect of single coolants. The coolants, which may be used in these compositions, are well known in the art and may be obtained commercially or through a known process. Suitable coolants include, for example, menthol, N-ethyl-p- methane-3-carboxamide (WS-3), N-2,3-trimethyl-2-isopropyl butamide (WS-23), 1- menthone glycerin ketal, 3-1-menthoxy propane- 1,2-diol or monomenthyl succinate or its salts. Such compositions, as well as the amount of mint flavor or aroma to add to these compositions is well known to one skilled in the art. The mint flavor and aroma compositions may be used in a wide range of products and fragrances such as of foodstuffs, tobacco products, pharmaceuticals, oral care products, and sweeteners. Such products, as well as the amount of flavor or aroma to add to these products, would be well known to one skilled in the art. Especially preferred food products include confectioneries such as chewing gums. Especially preferred oral care products include mouthwashes or toothpastes.
EXAMPLES
A better understanding of the present invention and of its many advantages will be had from the following examples, given by way of illustration. Example 1
90.0 g Rectified Spearmint Oil
9.9 g Water
0.1 g Cysteine Hydrochloride
The above ingredients were added to a 500 ml round bottom flask equipped with a reflux condenser, mechanical stirrer and pot thermometer. The contents were heated over 20 minutes to a temperature of 104°C and the temperature held for one hour. The contents were cooled to room temperature and the phase separated. The treated spearmint oil was used as is. Example 2
0.1 g Treated Spearmint Oil (Example 1)
9.9 g Ethanol
A solution of treated spearmint oil from Example 1 was made by using 0.1 g treated spearmint oil with 9.9 g ethanol.
A similar solution was made of untreated spearmint oil. To a 10% sugar water solution, 0.1% of each solution was added. This delivered 10 ppm of both treated and untreated spearmint oil. Comparing the taste of both beverages showed that the treated oil was stronger in flavor, more fresh picked in character, and cooler than the control (untreated oil).
Additionally, all panelists remarked on the increase in sweetness intensity.
Example 3 90.0 g Peppermint Oil
9.9 g Water
0.1 g Cysteine Hydrochloride
The above ingredients were treated as in Example 1.
Example 4 Product of Example 3 was compared against the untreated product as in Example 2.
The treated peppermint oil was stronger, sweeter and cooler than untreated oil.
Example 5
90.0 g Carvone Fraction ex caraway oil (60% Carvone)
9.8 g Water 0.2 g Cysteine Hydrochloride
The above ingredients were treated as in Example 1. The product of Example 5 were evaluated as in Example 2. The treated carvone, product of Example 5, was sweeter, stronger in flavor, fresher tasting and surprisingly was cool tasting relative to the untreated material.
Example 6
Toothpaste Example #6
Sodium Fluoride 0.243
Sorbitol 59.202
Silica 20.000
Synthetic Sodium Alkyl 4.000
Sulfate (27.34% aqueous solution)
Buffers 2.040
Monsodium Phosphate 0.590
TiO2 0.525
Thickeners 0.775
Coolant lN-2,3-trιmethyl-2-ιsopropyl butamide 0.200
Coolant 2N-ethyl-p-menthane-3-carboxamιde 0.090
Saccharin 0.460
Spearmint Oil, Product of Example 1 1.000
Total 100.000
Toothpaste was cooler, sweeter and stronger in flavor than control toothpaste made with untreated Spearmint Oil.
Example 7
Toothpaste Example #7
Sodium Fluoride 0.243
Sorbitol 24.614
Silica 23.411
Synthetic Sodium Alkyl 4.000
TiO2 0.500
Thickeners 0.800
Glycerin 9.000
Tetrapotassium Pyrophosphate 6.382
PEG-6 3.000
Sodium Acid Prophosphate 2.100 Tetrasodium Pyrophosphate 2.050
Dye 0.050
Menthol 0.400
Coolant lN-2,3-tπ___ethyl-2-_sopropyl butamide 0.200
Coolant 2N-ethyl-p-menthane-3-carboxamιde 0.090
Saccharin 0.460
Peppermint Oil, Product of Example 3 0.800
Total 100.000
Toothpaste was cooler, sweeter and stronger m flavor than control toothpaste made with
10 untreated Peppermint Oil.
Examples 8. 9. 10. 11 Chewing gum compositions were prepared using the formulations set forth below. The formulations were prepared by melting the gum base at a temperature of about 85 to 90°C and then adding with mixing the lecithin followed by adding the corn syrup and
15 1/2 of the sugar and again mixing until homogenous mixture was obtained, approximately 5 minutes total time. The flavor and glycerin were then added and mixed for about 2 minutes each followed by the remaining sugar which was mixed until a homogenous mixture was obtained, about 2 minutes. The formulation was cooled to about 40 to 45 °C and the menthol and carboxamide compounds added and mixed into 0 the formulation. The formulations were then cut into slab shapes. These formulations were subjected to sensory evaluation studies to assess the perceived breath freshening of compositions.
Composition
Ingredient Ex.8 Ex.9 Ex.10 Ex.11
Gum Base 21.00 21.00 21.00 21.00
Corn Syrup 16.50 16.50 16.50 16.50
440BE
Sugar 6x 60.60 60.60 60.60 60.60
Lecithin 0.20 0.20 0.20 0.20
Peppermint Oil 1.1438 1.1438 Product of Example 3 — 1.143 1.1438
Glycerin 0.45 0.45 0.45 0.45
Menthol 0.1062 0.075
N-ethyl-p-menthane-3-carboxamide — — 0.1062 0.1062
Product of Example 8 had high up front cooling which dropped off after 2 minutes and bitterness developed.
Product of Example 9 had high up front cooling which maintained for 15 minutes without bitterness development. Flavor was also stronger than Example 8 with a lingering sweetness for 12 minutes.
Product of Example 10 had no up front cooling, however, cooling gradually developed after about 2 minutes.
Product of Example 11 had high up front cooling which maintained for 15 minutes without bitterness development. Flavor was also stronger than Example 10 with a lingering sweetness for 12 minutes. Example 12
90.0 g Fennel Oil
9.9 g Water
0.1 g Cysteine (free base)
The above ingredients were treated as in Example 1 and evaluated as in Example 2. The treated Fennel Oil was stronger in anethol notes, was sweeter and more cooling than the untreated material. Example 13
90.00 g Peppermint Oil
9.95 g Water 0.05 g Cysteine Methyl Ester The above ingredients were treated as in Example 1 and evaluated as in Example 2.
The treated peppermint oil was stronger in peppermint flavor, sweetness and coolness than untreated peppermint oil.
Example 14 90.00 g Rectified Spearmint Oil
0.10 g Cysteine
9.90 g Water
The above ingredients were treated as in Example 1 and the product evaluated as in Example 2. The product of Example 14 was stronger, sweeter and cooler than the untreated oil and was similar in character and strength to the product of Example 1.
The above description of the invention is intended to be illustrative and not limiting. Various changes or modifications in the embodiment described may occur to those skilled in the art. These can be made without departing from the scope and spirit of the invention.

Claims

What is claimed is:
1. A mint flavor or aroma composition comprising a treated mint oil, flavor or aroma obtained by mixing a mint oil, flavor or aroma with a cysteine source selected from the group consisting of cysteine, a salt or ester thereof, a cysteine precursor and a cysteine derivative and, optionally, a solvent.
2. The composition according to claim 1 where in the treated oil is peppermint oil.
3. The composition according to claim 1, wherein the treated oil is spearmint oil.
4. The composition according to claim 1, wherein the mint flavor is a natural flavor.
5. The composition according to claim 1, wherein the 1 mint flavor is an artificial flavor
6. The composition according to claim 1, wherein the source of cysteine is cysteine or cysteine hydrochloride.
7. The composition according to claim 1, wherein the treated oil is rectified spearmint oil, the source of cysteine is cysteine hydrochloride and the solvent is water.
8. The composition according to claim 1, wherein the treated oil is peppermint oil extract, source of cysteine is cysteine hydrochloride, and the solvent is water.
9. A coolant composition comprising the composition according to claim 1 , and at least one cooling material.
10. The coolant composition according to claim 9, wherein the cooling compound is selected form the group consisting of menthol,
N-ethyl-p-methane-3-carboxamide (WS-3), N-2,3-trimethyl-2-isopropyl butamide
(WS-23), 1-menthone glycerin ketal, 3-1-menthoxy propane- 1,2-diol and monomenthyl succinate or its salts.
11. A food product, a tobacco product, or confectionery which comprises a composition according to claim 1.
12. The food product according to claim 11, wherein the confectionery product is a chewing gum.
13. An oral care product comprising a composition according to claim 1.
14. The oral care product according to claim 13, wherein the oral care product is a mouthwash or a toothpaste.
15. A pharmaceutical which comprises a composition according to claim 1, and a medicament.
16. A topically applied pharmaceutical which comprises a composition according to claim 9, and a medicament.
17. A sweetener which comprises a composition according to claim 1.
18. A fragrance which comprises a composition according to claim 1.
19. A fragrance which comprises a composition according to claim 9.
20. The composition according to claim 1 wherein the composition is encapsulated.
21. A process for preparing a treated mint oil, flavor or aroma which comprises which comprises mixing a mint oil, flavor or aroma with a cysteine source selected from the group consisting of cysteine, a salt or ester thereof, a cysteine precursor and a cysteine derivative and, optionally, a solvent.
22. The process according to claim 21, wherein the mixing occurs at a temperature from about 20°C to about 250°C.
PCT/US2000/031266 1999-11-15 2000-11-14 Mint flavor and aroma compositions WO2001035918A1 (en)

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US09/441,159 1999-11-15

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JP2009511682A (en) * 2005-10-14 2009-03-19 トーマス フランク ホフマン アンド アンドレアス ドゥンケル Onion flavor compounds and uses
US8865192B2 (en) 2006-07-07 2014-10-21 The Procter & Gamble Co Flavor oils with reduced sulfur content and use in oral care compositions
US9089163B2 (en) 2010-12-01 2015-07-28 Tobacco Research And Development Institute (Proprietary) Limited Feed mechanism
US9155769B2 (en) 2006-07-07 2015-10-13 The Procter & Gamble Co Flavor oils with reduced dimethyl sulfoxide content and use in oral compositions
US9462828B2 (en) 2009-03-09 2016-10-11 British American Tobacco (Investments) Limited Apparatus for introducing objects into filter rod material
CN109777613A (en) * 2019-02-22 2019-05-21 深圳烟草工业有限责任公司 A kind of cigarette Mint Essence
RU2724996C2 (en) * 2015-06-30 2020-06-29 Вм. Ригли Джр. Компани Cooling compositions of long action
US20210315178A1 (en) * 2020-04-10 2021-10-14 Wild Flavors, Inc. Columbia

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US9462828B2 (en) 2009-03-09 2016-10-11 British American Tobacco (Investments) Limited Apparatus for introducing objects into filter rod material
US9089163B2 (en) 2010-12-01 2015-07-28 Tobacco Research And Development Institute (Proprietary) Limited Feed mechanism
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RU2724996C2 (en) * 2015-06-30 2020-06-29 Вм. Ригли Джр. Компани Cooling compositions of long action
CN109777613A (en) * 2019-02-22 2019-05-21 深圳烟草工业有限责任公司 A kind of cigarette Mint Essence
US20210315178A1 (en) * 2020-04-10 2021-10-14 Wild Flavors, Inc. Columbia

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